High school friend is an escort

[John Doe II]

So I noticed an ad a while back of a friend who i recognized from high school is now an escort. I'd love to meet him but his ad is gone now. We are friends on FB and i follow him on insta. Any recomnendations?

[+ Lucky]

A while back? The horse has left the barn! Your opportunity is gone. Your Facebook friend is not there as an escort, so I wouldn't approach him. Keep an eye out for a repeat of the ad.

[The_Impeccable_G]

So I noticed an ad a while back of a friend who i recognized from high school is now an escort. I'd love to meet him but his ad is gone now. We are friends on FB and i follow him on insta. Any recomnendations?

No need to contact him as an escort. Actually it may be better if you do not mention you saw his ad, even if you end up paying him for sex. He is your old friend from high school who may need a small "loan" Talk to him and see what happens.

[cany10011]

I think it would be quite a fantasy to hookup/rent one of my hot high school classmates...

[+ Gar1eth]

I remember I was once looking at the Data Lounge Site. And someone posted that there was an escort/porn actor whom he had gone to college with.

 

Gman

[+ poolboy48220]

I think if any of my high school friends were escorting now they'd have trouble at their age getting up from being on their knees

 

There were a handful of guys from high school that I would have gladly hired. I'd swear the quarterback was flirting with me in one of our senior year classes, but I was years away from being bold enough to pursue that.

[marylander1940]

So I noticed an ad a while back of a friend who i recognized from high school is now an escort. I'd love to meet him but his ad is gone now. We are friends on FB and i follow him on insta. Any recomnendations?

 

If noticed that a while back and his ad is down, maybe he used to be an escort and now has another job.

[+ Pensant]

Looking through my hs yearbook recently, I was amazed at how many hotties there were.

[marylander1940]

Looking through my hs yearbook recently, I was amazed at how many hotties there were.

 

The good thing about aging is that all of the sudden we're surrounded by SO many younger men...

[+ Pensant]

The good thing about aging is that all of the sudden we're surrounded by SO many younger men...

And I increasingly find all college age and 20ish guys hot!

[Keenan]

So I noticed an ad a while back of a friend who i recognized from high school is now an escort. I'd love to meet him but his ad is gone now. We are friends on FB and i follow him on insta. Any recomnendations?

 

Even if his ad were still up I wouldn't contact him. Unless he told you he was an escort I would avoid bringing it up or hiring him. You have a relationship as friends and if he is trying to keep this separate from friends and family contacting him on the premise of him being an escort could make things awkward.

[xyz48B]

@Keenan – I have to tend to agree with you. I could see that coming back down the road to haunt you if things sour between you – not that they necessarily will, but they could. If you hookup, that’s one thing. But the escorting thing is murkier and trickier.

[+ keroscenefire]

I hired one time and realized it was a someone I had met once before and shared many mutual friends and acquaintances. We ended up meeting a couple of times and actually he was a lot of fun. But of course you have to be very discreet and cautious. We actually met another time in public at an event organized by a mutual friend and I let him be introduced to me as if I never met him. It was kinda awkward but also sort of fun. I'd love to meet him again but I think he stopped escorting after the whole COVID thing though.

[+ poolboy48220]

I hired one time and realized it was a someone I had met once before and shared many mutual friends and acquaintances. We ended up meeting a couple of times and actually he was a lot of fun. But of course you have to be very discreet and cautious. We actually met another time in public at an event organized by a mutual friend and I let him be introduced to me as if I never met him. It was kinda awkward but also sort of fun. I'd love to meet him again but I think he stopped escorting after the whole COVID thing though.

There was an old thread a while ago about meeting someone socially that you'd previously hired. it's happened to me, I did just as you did; let myself be introduced. But I kept wondering if his boyfriend (who was at the social event) knew he escorted. I never asked, I think that'd set off red flags.

[NikoLeto]

I think this is very specific to the escort.

 

Across the handful of years I've escorted, I've taken friends as clients. My only concern is that they can keep the interaction secret to the broader spectrum of people we know. If you can find a way to approach, start by making it clear you don't intend on revealing the information to anyone else and that you want to make sure that the experience won't be awkward for them.

[+ Keith30309]

Jeesh, I sure wouldn’t want to hire anyone from my high school class. They’re all a bunch of old geezers.

[+ Gar1eth]

Jeesh, I sure wouldn’t want to hire anyone from my high school class. They’re all a bunch of old geezers.

 

Going by the 30 year reunion back in 2009 there are still a few I'd love to get naked with.

 

Gman

[+ nycman]

I agree. If there‘s not an active ad, let the fantasy fade.

 

At a very high brow benefit in NYC, I once ran into an escort I had hired.

He was the trainer of one of the mega corporate wife’s at the event.

As soon as he saw me, I saw the panic in his eyes that he might reveal

our secret and that he didn’t know how to greet me. When we were

formally introduced, I threw my arms open wide, screamed his real

name (which I didn’t know until that exact moment) and greeted him

like we were long lost best friends from the gym. I could feel his sigh

of relief as we hugged.

 

Crisis averted. He later sent me a text thanking me, and we’ve met

several times since. The lesson? It’s only awkward, if you make it

awkward.

[+ DrownedBoy]

It depends on how close you are. If you're just Facebook friends and don't really meet in person anymore, I'd say go for it. It's not like he's going to share that with anyone else.

 

You could approach him in a cute way, like confessing you had a crush on him in high school (even if you didn't), then bring up the ad. Make sure to act all embarrassed when you bring it up. He'll be flattered even if he turns you down.

 

I had masturbation candy in high school, but the purest memories of lust come from junior high, when I started puberty. But neither they nor I can go back to being that young.

[John Doe II]

It depends on how close you are. If you're just Facebook friends and don't really meet in person anymore, I'd say go for it. It's not like he's going to share that with anyone else.

 

You could approach him in a cute way, like confessing you had a crush on him in high school (even if you didn't), then bring up the ad. Make sure to act all embarrassed when you bring it up. He'll be flattered even if he turns you down.

 

I had masturbation candy in high school, but the purest memories of lust come from junior high, when I started puberty. But neither they nor I can go back to being that young.

I would probably say he was more of an acquaintance. We had a few classes together but didn't really hang out much. Just to clarify, when I said "a while back," I meant right before coronavirus. So it wasn't that long ago...

[John Doe II]

I think this is very specific to the escort.

 

Across the handful of years I've escorted, I've taken friends as clients. My only concern is that they can keep the interaction secret to the broader spectrum of people we know. If you can find a way to approach, start by making it clear you don't intend on revealing the information to anyone else and that you want to make sure that the experience won't be awkward for them.

I clicked like on some of his naughtier pics on insta. I don't even think he knows I'm into guys. ? If his ad pops up again, would it be too much of a surprise to schedule a meet? Or should I aproach via FB/Insta & not mention his ad until much later on?

[The_Impeccable_G]

I would probably say he was more of an acquaintance. We had a few classes together but didn't really hang out much. Just to clarify, when I said "a while back," I meant right before coronavirus. So it wasn't that long ago...

@John Doe II May I ask how long ago was high school? I am sure I would not have sex now with my old classmates. ?

[John Doe II]

@John Doe II May I ask how long ago was high school? I am sure I would not have sex now with my old classmates. ?

Within 7 to 10 years. ??

[The_Impeccable_G]

Within 7 to 10 years. ??

You are lucky. Just go for it. Don't overanalyse. Message him on insta/fb and see what happens. Be polite but direct. This is my advice.

[The_Impeccable_G]

You are lucky. Just go for it. Don't overanalyse. Message him on insta/fb and see what happens. Be polite but direct. This is my advice.

One more thing: Make sure he is hot as you remember him. That he did not gone bald, or put on weight etc. ?